Mens Watches: The Best Luxury Watches Under $1000, Plus What You Should (And Shouldn’t) Wear Them With



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Trying to find an affordable luxury watch? I can help.

android watch apple watch

First, let me start by saying there are 3 main types of men’s watches:

  • Dress watches
  • Casual watches
  • Sport watches

The best thing about a luxury watch is you get the creativity of art in a fashion-forward style, combined with the genius of engineering in a classically designed watch.

Luxury watches are made with the highest standards of quality, precision, and workmanship — making each watch a cherished heirloom.

Following are my best tips for choosing a luxury watch, what to wear with each of the 3 types of mens watches, and some examples of luxury watches that I feel will give you the most bang for your buck.

 

Mens Dress Watches

When I’m speaking of a dress watch, I’m referring to a watch that is strictly worn with a suit and tie.

marc jacobs leather watch

A man’s dress watch should be a lower profile and lighter weight watch — with a fine leather band.

The watch band’s leather should match the color of belt and shoe you are wearing.

 

What to wear with a black leather watch band:

  • A black leather band with black leather belt and black leather shoes can be worn with navy, gray, and black.
  • Black should never be worn with earth tones — such as brown, olive, and tan. If you believe black leather goes with tan then the next time you put on your navy, charcoal gray, or black suit don’t forget to lace up those white dress shoes to go with it. Respectfully, Elvis has left the building.

 

What to wear with a brown leather watch band:

  • A brown leather band with brown leather belt and brown leather shoes can be worn with navy, gray, brown, olive, and tan.
  • Brown should never be worn with black.

 

Examples of High-Quality Mens Dress Watches

Baume & Mercier rectangular watch with black leather strap and silver accents:

 

Baume & Mercier rectangular watch with brown leather strap and silver accents:

 

Raymond Weil watch with brown leather strap and rose-gold tone accents:

 

Raymond Weil watch with black leather strap and silver accents:

 

Tissot watch with a black leather strap and rose-gold tone accents:

 

Tissot watch with a brown leather strap and silver accents:

 

Mens Casual Watches

When I’m speaking of a casual watch, I’m referring to a watch that is worn with a sport coat or blazer with dress trousers.

mens casual watch dress watch

Almost all the same principles of what you would wear with a suit and tie apply with casual watches — with the exception of the following:

  • You can move to a higher profile and heavier weight watch that has a leather or metal band.
  • This is also where I prefer the chronograph watch — for a little more of a casual look that still remains smart and sophisticated.

I recommend that a gold metal band or brown leather band be worn with earth tones, as discussed above.

I know there a lot of men who like the look of a heavier sport watch, but unless you’re in the business of sailing, yachting, diving or water sports, a water-resistant dive watch is never appropriate with dress or casual clothing — no matter how luxurious the watch may be.

 

Examples of High-Quality Mens Casual Watches

Movado silver tone chronograph watch:

 

Movado gold tone chronograph watch:

 

Raymond Weil stainless steel watch with bracelet band:

 

Raymond Weil rectangular chronograph watch in stainless steel:

 

Tissot chronograph watch with a brown leather band:

 

 

Tissot chronograph watch with a gold tone bracelet band:

 

Mens Sport Watches

When I’m speaking of a sport watch, I’m referring to a watch that is worn with:

  • chinos and a button down collar shirt
  • denim and a 3-button polo
  • shorts and a t-shirt

mens sport watches

This is when you wear that sport watch that speaks to your hobbies or outdoor passions.

 

Examples of High-Quality Mens Sport Watches

Tissot blue silicone sport watch:

 

Luminox black stainless steel bracelet watch:

 

Victorinox Swiss Army silver tone chronograph watch:

 

Casio black synthetic resin watch:

 

I hope that my tips have helped you decide what would be the best type and style of watch for you — and gave you some ideas as to what to wear it with.

There are plenty of affordable luxury watches available online and in stores.

The watches listed above are examples of classically designed luxury brands and price points where I believe you may find the best value for your investment.

 

More About Mens Luxury Watches

In addition to the links I’ve included above, here are some other resources to help you choose your first luxury watch:

Steve Walczak

I've been in the men's clothing business since 1991. My specialty is custom-tailored suits and shirts, as well as men's accessories.

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